Hydrochloric Acid → HCID 18705807, compound

HRID 2287846Notes

Reaction equation

HRID 2287846 reaction equation
[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([OH:17])=[C:10]([C:14]([NH2:16])=[O:15])[CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][F:30].Cl>CN(C=O)C>[CH2:18]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:17][CH2:28][CH2:29][F:30])=[C:10]([C:14]([NH2:16])=[O:15])[CH:11]=2)[CH2:6]1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 18705820HCID 18705820, compound

Product 1

HCID 18705807HCID 18705807, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(Dipropylamino)-2,3-dihydro-6-hydroxy-1H-indene-5-carboxamide (87, 0.14 g, 0.5 mmol), potassium carbonate (0.2 g, 1.5 mmol), 1-bromo-2-fluoroethane (0.19 g, 1.5 mmol) in DMF (10 mL) was stirred at room temperature for 5 h. The mixture was quenched with water, and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated. Chromatographic purification yielded a pale yellow solid which was converted into the HCl salt and crystallized from EtOAc/MeOH to give the title compound 88 as an off-white solid (m.p. 232-233° C.).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customChromatographic purification
  8. customyielded a pale yellow solid which
  9. customcrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-25a8bb1697104658a804df5c8f6e0cb3
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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